Categories: C-S Bond Formation >
Synthesis of thiophenols
Name Reactions
| Two Steps: |
Recent Literature
A CuI-catalyzed coupling reaction of aryl iodides and sulfur powder takes place
in the presence of K2CO3 at 90°C in DMF as solvent. The
coupling mixture is directly treated with NaBH4 or triphenylphosphine
to afford aryl thiols in good to excellent yields. A wide range of substituted
aryl thiols that bear methoxy, hydroxyl, carboxylate, amido, keto, bromo, and
fluoro groups can be synthesized.
Y. Jiang, Y. Qin, S. Xie, X. Zhang, J. Dong, D. Ma, Org. Lett., 2009,
11, 5250-5253.
CuI-nanoparticles catalyze a selective synthesis of phenols, anilines, and
thiophenols from aryl halides in the absence of both ligands and organic
solvents. Anilines were formed selectively with ammonia competing with
hydroxylation and thiophenols were generated selectively with sulfur powder
after subsequent reduction competing with hydroxylation and amination.
H.-J. Xu, Y.-F. Liang, Z.-Y. Cai, H.-X. Qi, C.-Y. Yang, Y.-S. Feng, J. Org. Chem., 2011,
76, 2296-2300.
